Tactical fundraising by Elizabeth Yin

People often ask me what startups I want to fund.  I hesitate to write this list because I’ve found there’s actually very little correlation between areas that I would love to fund and what I end up funding.  This is because beyond business ideas, there are so many factors that make a great business.

For example, in 2018, I’ve championed and completed 7 deals at Hustle Fund.  Coming into 2018, because I was/am seeing so many blockchain and health companies, I thought I would fund mostly blockchain and health companies.  It turns out, I have done 0 health deals in 2018 (I did 3 in 2017), and I have done 2 blockchain deals.  In other words, the majority of the deals that I have done this year are not in either category.

That being said, these are the areas or problems that I’m interested in funding, all other considerations aside:

Health

Our medical system is a huge f***ing mess.  I am looking to fund ideas that will make big changes here.  In particular:

Health Insurance:

Health insurance is the biggest scam ever.  Because health insurance is tied to your employer (which makes no sense from a societal perspective), you as the consumer, are at the mercy for what your company thinks is best for you.  As a result, you don’t actually get to vote with your dollars which doctor you choose or which services you want done.  This means you will over-visit the doctor and clog up our medical system if your employer gives you a low deductible plan  (and rightly so – from an economics perspective, you should take advantage of this). It also means that you will be tied to horrible health care providers if your employer bought a cheap plan with a limited network.

So, let’s change this up.  I’m most interested in funding completely new health insurance models that give power back to the consumer.  Things like health savings accounts – you get to decide whether you would prefer to keep your cash as an investment or go see the doctor.  I like the general direction that Lively seems to be going in.  Or direct primary care plans – you should be able to decide which service providers to pay for, and they should be on the hook for drumming up their own business and serving patients well.  You also shouldn’t have to get a referral from another doctor to be able to see a specialist weeks later for an issue that needs to be addressed today.  Money or credits of some type should allow you to prioritize your situation when you’re in a bind.  These days, it seems that connections to doctors are more important than anything else.

Providers:

We have a shortage of internal medicine physicians and nurses in this country.  On one hand, it’s great that we have a lot of certifications to enable our medical professionals to be properly trained, but if I’m going to be forthright, the medical system is really just a cartel.  We need to increase the number of people who have some basic medical knowledge to help alleviate the strains of our bogged-down medical system.  I’m interested in ideas that take advantage of geography – can you see a doctor today who is in the midwest somewhere (virtually) or even overseas somewhere, where there are more medical professionals?  We are starting to see some doctors who are licensed to practice in California live abroad in Bali and partake in telemedicine – can we do more of this to help with patient loads from state to state and perhaps get more doctors certified in multiple states?  Or perhaps it’s a tech-enabled service in itself – I like the direction that Carbon Health appears to be going in.

Costs:

I’ve seen a lot of startups attempt to reduce medical costs.  90% of medical costs are attributed to about 10% of patients.  So, even though in the US, our medical costs have really ballooned, I’m actually less concerned about optimizing the costs of the remaining 90%.  There are all kinds of startups trying to address different ways to track the sick and the elderly and encourage preventative measures and reduce costs.  But it’s a hard problem to solve, and I’m still looking to make a bet here because I haven’t quite found a solution that I’m bought into that I think will really solve this problem.

As a sub-category of health, I’m also really interested in startups changing women’s health.  I think we still have a long way to go when it comes to contraception, fertility, and postpartum care.

This an area that I’m incredibly bullish on and yet at the same time find really difficult to fund because often solutions in these space require hardware, new devices, and FDA approval (all areas that I tend to shy away from as a small fund).  There are a few trends that I think fit into this space.  Women are delaying having children, which means that we as a society need to embrace new forms of contraception (not sure this is something software can solve) to improve reliability, usage, and side effects.  One of our portfolio companies called The Pill Club, for example, sends women birth control right to their doors.

The flip side is that we are now also seeing a number of women go through IVF.  I think we are in the first inning of what this looks like, and again, I’m doubtful that software can solve this actual problem.  But, I can see how there may be opportunities to use software to increase the chances of success of IVF – perhaps through better data analysis – or help women receive the care they need through telemedicine and consultation.

On the post-child front, there are a lot of women-specific issues.  Postpartum care and depression, as a result of having a child, is a real and is a serious problem.  A postpartum care platform called Mahmee is tackling this by using software to help new moms get the support they need online from professionals.

Childcare

Speaking of children, childcare is a topic in itself that affects all parents – not just moms.  Childcare is expensive.  One thing I noticed in living in an area with a high cost of living is that your expenses go up dramatically once you have a child.  Even if you’re not sending your infant to the “Harvard of daycare”, your monthly expenses for 2 children under 5 years old can easily be an extra $3000 per month if not a lot higher!  On the other hand, the people who need to send their children to daycare the most are people who need to work and can’t afford to stay at home.  So it’s a bit of a catch 22.

I’m interested in exploring very different childcare models.  For example – some wild ideas:

Daycares are a supply and demand issue – in higher cost areas,

• Is it possible to load your toddler up on a bus and bus your kid out to a daycare 2 hours away where the facilities and cost to run them are a lot cheaper?  I’m sure this is fraught with all kinds of problems including obtaining necessary licenses, and heaven forbid what would happen if said bus got into an accident.  But, it’s an interesting question to explore, because in the coming years, I expect transportation to get cheaper / reliable (more safe) / autonomous or semi-autonomous.
• Is there a way to increase the use of home daycares?  Why are many parents reluctant to use home daycares?  Because of potential negligence of the sole-provider of home daycares?  Is there a way to add video technology to add checks and balances to make sure that your kid is being cared for?
• Is there a way for employers to provide loans for early childcare?  I.e. for 4-5 years, parents in high cost areas shell out $10k-$40k per year just on childcare per child.  And then at kindergarten, public schools are basically free for the next 13 years.  Is there a way to spread this cost of say $40k-$200k across time while simultaneously improving employee retention?

I’m not sure if these ideas are any good, but I think childcare or the way to fund childcare can be completely reimagined.

Work

The workplace is changing a LOT.  In particular, I’m most interested in funding ideas that further entrepreneurship and being entrepreneurial.  These days, everyone is an entrepreneur.  Whether you are starting a mom and pop business or a tech startup or are getting into freelancing / consulting or are joining the gig economy, you are an entrepreneur even if you never thought of yourself as one.  When I was a child, being an entrepreneur was basically limited to tech startups and restaurants and salons.  These days, you see doctors and lawyers doing virtual consultations and living in Bali.  You see students, immigrants – everyone really – driving cars, returning scooters, and renting out their homes to make some extra money.  You see stay-at-home moms making crafts to sell on Etsy and Shopify.

With Hustle Fund, this year, I’ve backed a banking service for freelancers called Every Financial.  And I’ve backed a back ops platform for freelancers called Hyke.  I’m very interested in this category overall – whether it’s new ways to make money or tools to help support new entrepreneurs, this is a category I’m bullish on as a whole that is only growing.

Education

Education is an area that is so incredibly important but is often a very tough to make money in.  I’m most interested in ideas that can enable students / graduates to make a livelihood.

For example, people are changing jobs more than ever and need the skills to do this.  I’m interested in new forms of education that will help people get the skills that they need to switch careers faster.  For example, we have backed Kenzie Academy, which helps teach people to become developers in cities where this education is traditionally not available.  But, I don’t think everyone needs to become a developer.  There are lots of jobs that could use more skilled people.  Can you use VR to teach new skills that require your hands?  Is there a way to teach people sales online?

At younger ages, I think that there are opportunities here as well to both teach and offer compensation.  In the old days, we had apprenticeship models.  Could the replacement for colleges and universities look more like an apprenticeship?  Instead of spending $500k on college, can you break-even for your education by working while learning?  For example, as a business major, can you take classes on lead generation?  Outbound sales?  And also some theoretical ones on game theory and pricing?  And can you intern at Salesforce to pay for your education in a co-op fashion during the year?  Minerva is doing some incredibly interesting things here, and what is amazing to me is that in just a short period of time, high school students are clamoring to go to Minerva.  They rank up there with the Ivy Leagues et al.  And I think there can many more schools that can be established with a differentiated approach to drive the cost of education down for young people.

At an even younger age, can you do the same thing for high school summer programs?

Education in this country is broken, but I think we can start approaching this by providing better programs that center around livelihood and job placement.

Housing and commuting

Housing is an issue that is near and dear to my heart.  In the San Francisco Bay Area, we have a massive problem with housing.  We don’t have enough housing supply.  And, we have terrible restrictions in many places in California that prevent us from building up – this is why you don’t see skyscraper apartment buildings around here unlike in NYC.  This means that people’s commutes around here are really long – in some cases, people commute 2-3 hours from outside the Bay Area each way to work here.  And rents are astronomical.  This isn’t sustainable.  I really don’t know the right way to approach this, but this is a problem I think about a lot.

Decentralized and verified data

We are funding a lot of blockchain companies attacking many different problems.  Here are a couple of broader trends that I’m a big fan of.

1. Decentralized data / crowdsourcing of data / verification of data

This has mass implications everywhere.  Tracking people (refugees, drug addicts, professional credentials, etc.) in order to better help them.  Tracking objects (validating scarcity, validation of the creator, verification of ownership).  Tracking information of the crowds.

For us as a fund, the tricky thing about this category is that the business model is a bit rough / not straightforward.  But, I’m seeing interesting business models, where companies insert themselves in transactions (that involve validating things or providing services).  The scope can also be tough – i.e. does your business need to aggregate massive amounts of data in order to be useful to other people?

2. Decentralized Marketplaces

I’ve written a whole blog post about this here.  Basically, this makes sense where there’s a dumb middle(wo)man who takes a massive cut for doing little to no work.  Or there are payment transactions that involve lots of fees today because there are cross border or cross currency payments but using cryptocurrency, this can all be avoided.

3. Tools and protocols

Blockchain is in the first inning of this baseball game.  There are a lot of tools, platforms, and protocols that need to be built to make it easier for developers and startups to build companies.  Much like how in the 90s, a startup would need $5m just to get a server going in a closet, blockchain also is in that same era.  I am interested in funding tools and protocols to make development and spin-up of new blockchain companies easier.

These are some of the problems or opportunities I’ve been thinking about lately.  But, A) they could turn out to be horrible businesses since I haven’t done the customer development on any of these, and B) as I mentioned before, the vast majority of companies I fund are not necessarily chasing any of these opportunities.

Cover photo by Sharon McCutcheon on Unsplash

Early stage fundraising is an interesting beast because there are all kinds of reasons why VCs invest at this stage.

Some background

There are essentially two camps of investors: a) those with a concentrated portfolio and b) those with a large, diverse portfolio.

Diversified portfolios:

Funds like YC, 500 Startups, and Techstars all have diverse portfolio strategies.  They invest in lots of companies.  Say, on 100 companies in a given portfolio, there may be a lot of losses, but a portfolio of this size only needs a couple of outsized winners to not only make up for the losses but also to return great multiples for the overall fund.  Because downside risk is mitigated by investing in a lot of companies, funds that utilize diverse portfolio strategies often have consistent results fund after fund – there isn’t as much variation across funds as you might see with a concentrated portfolio.

Concentrated portfolios:

Funds like Sequoia, A16Z, and Benchmark all have concentrated portfolio strategies.  They invest in few companies, so there’s little room for error.  Of course, any outsized winners will make the overall fund really, really fantastic because there are not that many losses for which to compensate.  These funds tend to have high variability across the industry.  Certainly there are top tier funds who are able to consistently return solid multiples fund after fund, but there are also many, many more funds who can’t even return 1x because the variability in this model is very high.  In other words, compared to the diversified portfolio model, this model is much higher risk and higher reward (for better or worse).

A couple of thoughts:

1. Some funds invest early to capture more ownership.  Others want to buy an option.

This is a point I didn’t fully understand until I became an investor.  Because large Sand Hill VCs largely make their money on a concentrated portfolio strategy, they need be really, really confident that their investments are going to work out.

By the time startups get to the series B level, it’s fairly clear whether a business is working and printing money.  Hot companies are highly sought after.  It’s very competitive to try to win a hot series B deal because every investor is chasing the same company.  As a result, there are a lot of large funds that will essentially buy a much smaller option at the series A level to be able to get potential access to a hot series B deal.  If some of those series A deals don’t turn out to be excellent businesses, then it’s just a small amount of money relative to the fund that didn’t work out.  If there is a hot deal in that group of series A deals, then it provides access to pour in tons of money and make a lot of money at the series B level.  Funds that make their money on later stage deals and who only invest at the earlier stages to buy an option don’t care so much about valuation.  They are only trying to buy a seat at the table to invest a lot in your company later when it’s clear you’re a winner – they are not trying to buy any ownership now.  

In the past couple of years, series B deals became way too hot and competitive.  A number of big funds have come down to invest at the series A to increase their optionality on capturing winners at the series B level.  Now that seed and series A are starting to bleed together, you are now seeing some large Sand Hill VCs do seed deals again.

In contrast, microfunds (small funds) largely only invest at the earliest stages (seed stages) because their money only goes far at these stages.  For most of these folks, they are trying to capture as much ownership at the earliest levels because they do not have more capital to invest at the later stages.

2. In general, microfunds are more valuation sensitive than bigger funds

As a result, because microfunds are trying to capture most of their ownership in a company at the earliest stages, they are going to be much more sensitive to valuation than a fund that is just trying to buy an option to invest in you in later rounds.  I’ve noticed that this can be a difference of as much as 2-3x on valuation caps!

In general, funds that do fewer (or no) follow-on checks will be more sensitive to valuation because they really only have one or two chances to buy as much of your company as possible.

Obviously, from an entrepreneur’s perspective, valuation is an important consideration, but it’s not the only one.  Even though larger funds will tend to be willing to invest at higher valuations, there is also more signaling risk that comes with an investment that is perceived as an option-investment.  In other words, if a fund invests in your company, if they typically make their money on series B rounds, and if they don’t invest in your series B round, many investors will wonder what is wrong with the company.  In contrast, no one cares if a small microfund doesn’t follow on because they don’t have the capital to do so and are not known for doing so.

So hopefully this provides some context as to how investors of big and small funds are thinking about your valuation.  Ultimately, valuation is really a matter of supply and demand, as I’ve written about before.  If no one is demanding your round, then it’s a moot point.  If everyone wants in, no matter how valuation-sensitive the microfund, they may get swept up in clamoring to invest in your round.

Cover photo by Kody Gautier on Unsplash

I took a look at how we invested in 2017 and thought I’d share some surprising and some not surprising findings.  I realize that investors are often a black box; it’s hard to understand what they prefer and what their biases are.  Hopefully sharing some of these stats will help illuminate what we care about.

Note: these stats are based on first checks we did in 2017 under Hustle Fund; I did not include follow-on checks.

1. We invested in many places but not in enough places.

Our mandate is to invest in US/CAN entities, so almost all of our investments are concentrated in the US and Canada (except for 1 company).  All are legally incorporated in the US and Canada.  Here’s the breakdown from last year:

Some quick thoughts:

1. We invested in way more Bay Area companies than we had anticipated.
2. We made no CAN investments!  :(
3. Though we did not do any investments in TO/Waterloo, Atlanta, Boston, or really anywhere in the midwest in 2017. We have done a TON of investments in these locations in the past and will likely look heavily there in 2018.  A big reason for this skew is that we’d known a few companies – either colleagues, friends, or founders we’ve worked with before – whom we wanted to back right out of the gates.  In the long run, however, on this fund, I expect the Bay Area to consist of around 35-40% of our investments.

2. Almost half of our companies have at least one female founder.

47% of our portfolio companies have at least one female founder.  In most cases, she is the CEO.  Although this is probably better than most VC portfolios, in the long run, I think we can still do better.

Note: for this stat (as well as the next one on race), we asked our founders to self-identify.  What I would love to understand, though I think it’s impossible, is what the overall funnel looks like.  I can’t tell you if 47% is actually a good number or not because I don’t know what percentage of the companies who are pitching us have at least one female founder (we do not ask about gender or race of our applicants).

That being said, my intuition is that the vast majority of pitches that I get have at least one female founder.  I don’t know if that is because my networks are different from Eric’s or if women prefer to pitch to female investors.  Maybe it’s purely coincidence.  I suspect there is something interesting here, and you could make a strong case for having funds run by GPs of different backgrounds and networks.

Lastly, pitches that start out with, “I am a female founder,” actually make me think that a founder doesn’t know how to run a business.  Investors are in the business to make money; I really don’t care about how you identify, as insensitive as that sounds.  I’m doing this to make my investors money (and hopefully some for me too :) ).  Here in the US, green is always green.

3. The racial diversity in our portfolio is OK but could be a lot better.

Again, these stats are based on self-identification.  One thing I noticed is that our mixed-founders identify as “other,”so if someone is, say, half Black and half Asian and identifies as “other,” he/she does not get included in any of the below stats.

• 20% of our companies have at least one Black founder.
• 7% of our companies have at least one LatinX founder.
• 53% of our companies have at least one Asian founder.
• 53% of our companies have at least one White founder.
• None of our founders identify as Native American.

I am happy with this start, and our portfolio is probably better than most VC portfolios, but I’m sure we could do a lot lot better and have a number of efforts planned for later this year.

Again, I would’ve loved to have examined the pipeline of companies we looked at but did not invest in, but this is just not logistically possible.

4. We do not always meet our founders in person.

In 27% of our investments, we still have not met the founding team in person.

I think this is pretty unusual for most VCs.  There are a few premises of why this is possible:

• I’ve hired a lot of remote folks before for my startup, so remote-coaching, which is a lot less hands-on, certainly works
• This allows us to invest in geographies where we are not physically located
• You don’t actually really know-know people based on location; it’s based on time and interactions
• Business success is based on results, and I can see that in other ways

In addition, I usually try to have most of my initial conversations with people over email before we hop on a call.  This is a tip I learned from my mentor David Hauser (founder of Grasshopper, acquired by Citrix) who actually invested in my company LaunchBit over email!  It’s a lot more efficient to cut to the chase and not waste anyone’s time in an email, and I can send a quick email with a couple of questions at midnight.

I suspect, but have no data, that this process of first talking concretely about a business over email and then moving people to a phone call actually removes a lot of unconscious biases.  I have no idea what people look like or how they dress or if they’re pregnant or whatnot.  Again no proof, though.

What I ultimately care about is speed of results.

5. We skewed towards B2B companies.

As I’ve mentioned in a prior post, we are certainly biased towards B2B companies!

43% of our companies are B2B companies, but even the companies I’ve put into other categories are also either B2B SaaS companies OR have a B2B partnership model to get consumers.

I’m not sure whether stating this will either attract more B2B companies or deter consumer companies, but regardless, I thought that I would mention this stat.  We do try to keep an open mind going into all deals, but clearly we have our biases.

In 2018, though, I can tell you right out of the gates that we’ve been doing so much more in blockchain.  So, we’ll see a bit of a sector skew.

6. We invested very early in 2017.  And love Lean Startup 101.  

60% of our companies were extremely early (e.g., product was rudimentary, concierge-based MVP, etc.), but a common characteristic of the companies we backed was having sales despite having essentially no product.  Many of these founders hustled sales before having a strong or fully-fleshed out product.  You might assume that the typical Hustle Fund founder profile is sales or marketing oriented, but this isn’t necessarily so.  Some of these teams only have product or engineering founders, but the impetus behind having a limited product is to make sure that you’re constantly learning from customers and users and that you’re only building out what they want, resulting in faster iterations.

Essentially, we really like founders who are very good AND FAST at the Lean Startup Methodology.  This is something we are quite biased towards: getting results even before having a full-fledged product to inform product decisions.

As I’ve written about before, 2018 is a different fundraising landscape (and still changing!).  We are looking for more traction in our 2018 investments in most categories than we were in 2017.  This is partly because our founders will need to achieve more in order to get to their next round.  By investing too early with such a small check, there’s a long time span between our check and the next round. As a small investor, we need our companies to get to the next round with very little capital.

Hopefully these stats are illuminating.  In 2018, I think we will see a lot of changes along geography and race as we ramp up our own activities.  We will likely see little to no changes along gender lines.  I suspect we will also see some changes in sector (more blockchain & health) but still tons of B2B in one way or another.  Probably lots of changes in traction levels as well.   We’ll see at the end of this year!

Cover photo by rawpixel on Unsplash

One of the reasons I started this blog in the first place is that I think the process of raising money is a black box.  I think we’ve made a dent in getting information out there, but at the pre-seed level, it’s still fairly unclear what investors are looking for. How do you assess a company when there is nothing or not much to show?

I can’t speak for other VCs, but here’s what I’m looking for:

1. What is the problem you are trying to solve and for whom?

I can’t stress this one enough.  This is probably the single most important thing to me, but as I mention here, it’s probably the number one area that entrepreneurs prepare the least for.

I’ll give you an example with my own startup, LaunchBit, and how our understanding of the problem and the customer became more refined over time:

V1: Helping online marketers get customers profitably.

V2: Helping online marketers who have previously bought ads in email lists get customers profitably.

V3: Helping directors of marketing at series B companies who have previously bought ads in email lists get customers profitably.

V4: Helping directors of marketing at series B B2B SaaS companies who have previously bought ads in email lists get customers profitably.

V5: Helping directors of marketing at series B B2B SaaS companies who have previously bought ads in email lists and are doing lead generation for free trials / webinars / and content get customers profitably.

At the pre-seed stage, a big way to stand out is if you have a V3 statement (as opposed to a V1 statement).

The way you get to a V3 statement is to start running the business and charging customers.  Almost all of the companies in whom we invested in 2017 had customers, even if they didn’t have much of a product.  Those who didn’t have a product or much of a product used a concierge model à la Lean Startup philosophy to start running their business.  By just getting started and exchanging money, you can learn more about your customer persona, his/her daily life, and what makes him/her buy.

Another way to get to a V3 statement is to have been in the industry before and to have experienced the problem you are trying to solve.

At the V3 level of understanding your problem and the customer, you will still have lots of questions and potential customer segments who could be a good fit for your product.  We are not looking for all answers to be resolved, but the presence of a narrowed scope is a big divide between those who are ready for pre-seed funding and those who are not.

Although this post is specifically about what I look for, every investor (including pre-seed investors) looks at this question.

2. What is the business model and the potential unit economics?

This one is pretty investor-specific.  Certain investors tend to gravitate towards certain business models.

“Five ways to build a $100 million business” by Christoph Janz at Point Nine focuses more on the market size, but it gets at business models indirectly and is a very good post to read.

At a high level, business is simple! :) You bring revenue in and your costs send money out the door.  You want your revenue to be higher than your costs.

But the execution is hard.  Do you spend lots of time going after big money (enterprise customers)?  Or spend virtually no time going after small money (à la Facebook)?  Or in between?  When you’re talking with an investor, I’d say in general, he/she has biases towards the customer acquisition methods that have made him/her money before. If he/she made money on pure consumer businesses, then he/she will gravitate more towards swatting flies (see Christoph’s post).  And, if you have a business that involves getting lots and lots of consumers onboard to pay small amounts of money, that is probably the type of investor you want to work with anyway because he/she will have insights from past learnings and dealings with other companies.

For me, I’m very much in the deer-hunting category, according to Christoph’s post. I’ve also done some rabbit deals.  Investors have their biases towards certain business models based on past experiences, and my biases are based on running my company LaunchBit (which was a deer-hunting model) as well as the companies I’ve funded over the last three years.

The reason I like deer-hunting businesses is that from my own experiences, I can see a clear path to bring in sales profitably.  You charge a high enough (i.e. high lifetime value) price such that you can get customers through partnerships, outbound sales, and/or lead generation + inside sales, which generally also have some fair cost to acquire customers.  It’s not so high that only a small number of people can pay for it, and so you don’t have to get the sales process perfect as a first-time entrepreneur or be a super salesperson.  I understand the nitty gritty operations required to do these customer acquisition methods, and that gives me conviction that with the right team, this type of business can fly.

On the flip side, I am definitely the wrong person to help with a fly business.  I know nothing about viral marketing.  I don’t know how you get that many customers at scale without spending a lot.  I’ll pass on those companies because I don’t understand these types of businesses well enough to get involved.  It certainly doesn’t mean these are bad businesses!  Facebook, Twitter, and Snap are proof of that!  It just means I’m the wrong investor-fit.  I’ve also passed on a lot of mice and elephant companies, too, because the unit economics feel too difficult to me.  This is because I just don’t know how to get customers profitably this way.  However, there are lots of investors out there who do know how to do enterprise sales or how to get lots of small customers at scale.

There are cases where I’ve ended up becoming an elephant or a mouse (or a fly) investor, but that’s been in situations where either the entrepreneur clearly knows how to get these customers (i.e., is an excellent marketer) or the company has pivoted.

Now here’s the thing: at a given firm, each individual investor has his/her own biases.  If a fund has a champion model (which we do), when an individual at a fund decides to invest, the fund invests.  If an individual at a fund passes, the whole fund passes.  So, if you can, you’ll want to chat with the person whom you think is best aligned with your company.  All too often, entrepreneurs try to pitch someone at a fund to build rapport based on external factors – such as gender; e.g., female entrepreneurs tend to pitch me more than Eric.  Or if you went to the same school as one of us.  Or grew up in the same town.  I think business-model-gravitation should be a bigger factor in whom you decide to pitch (how has this investor made money before?).  He/she will certainly be biased towards that.

I can’t speak for my business partner Eric, but he has had a lot more experience with building businesses and side projects with smaller lifetime values.  So if you have a mice-business model, you might be better off trying to pitch him than me.

3. Can I get behind the thesis?

At the pre-seed level, all investment decisions for all firms and investors are driven by thesis-alignment.  In other words, have I bought into the idea that this is a real problem and have I bought into this potential solution?

Here’s a concrete example of what I mean: when I was pitching LaunchBit, we started out as an ad network for email.  All the investors I pitched who believed that email was dead didn’t invest.  All of the people we pitched who became our investors had at least one other portfolio company that was doing something in email.

At the pre-seed stage, there is no way to prove that your thesis is right or wrong.  If an investor isn’t onboard, just move on quickly.  That’s ok.  In fact, the best companies are the ones with strong theses.  It also means that potential investors will be very bifurcated in their opinions.  Let me give you a few examples of companies that have strong theses that are very bifurcating:

AirBnB – investors either believed people would sleep on other people’s air mattresses or not

Uber – investors either believed people would ride in other people’s cars or not

Those van companies that double up as hotels – investors either believe that people are willing to do this or not

Anything bitcoin – investors either believe that bitcoin (or other cryptocurrencies) is massively undervalued or should go to zero; I don’t know anyone who thinks the status quo is here to stay

Investors are going to be wrong in their theses.  So, just because someone isn’t onboard because of your thesis, that doesn’t mean it’s a bad thesis.  It’s a matter of finding the right investor who agrees with it.

4. If sh*t hits the fan, can the company survive (and grow) on my $25k check?

As a small pre-seed fund manager, I have very different concerns from the Sand Hill VCs.  The Sand Hill VCs will support you in every round (if they think you’re good).  Me, I will write a $25k first check.  I might write another check later, but it won’t be that big, and I certainly don’t have enough money in my fund to lead your next round.

As a result, I won’t be a signaling risk to you, but it also means that I have to think a lot about downside risk.  If you are in a really competitive space where it will take a lot of capital to compete and outspend everyone, I might decline to invest.  I certainly understand that often it’s the 8th player who comes in and wins (e.g., Google and Facebook), but I don’t have the capital to play in those games.  This comes back to investor fit – the big firms are much better poised to fund these highly competitive spaces, not small firms like mine.  That being said, most of the time, entrepreneurs don’t know if they are in a competitive space or not until they start fundraising.  So if you start raising money and you hear from a few investors that your “space is too crowded,” you might want to think about how it informs your fundraising strategy.  It might be difficult to raise money at the early stages because most investors in the seed space have smaller funds (especially pre-seed funds).  Once you get to breakout success, raising money from the bigger Sand Hill funds could be easier.  So you might think about how to best poise yourself to bootstrap and get to profitability for the next couple of years.  Chances are, if three investors tell you that your space is “crowded,” this is a good proxy for what most investors think;  smaller funds will be harder to bring onboard.  Your wildcards for external funding at the pre-seed stage are angel investors – generally people who know you and are betting on you (and the less active ones may also not see enough deals to know whether a space is crowded :) ).

In addition, going back to #2, I have to believe that you can make money pretty early in your business life in case no one funds you again (or for a while).  My $25k check isn’t going to last long.  Bonus if my coaching can help you escalate that, but the business model itself has to print money immediately.  Long sales cycles or signed contracts that won’t pay you for months is tough as a small investor (see elephant hunting).  Similarly, consumers who pay you $5 per month need to be coming in droves in order to get you significant sustainable revenue.

5. Lastly, and most importantly, does the team execute with speed?

This is specific to what I look for and not other investors, per se, and I want to clarify what it means to execute with speed.  This means that you are making fast progress on the top thing that matters.  For most companies, this is usually sales.  In some cases, product and technology.

Let me give you a couple examples of companies that we backed who impressed us:

My first investment on this fund: CEO started selling to top tech companies even while it was a side gig and even before she had a product.  She did about $10k in sales that first month.

Another investment: Co-founding team started selling in-person at 5am to their target demographic (that was up at that hour) and hacked together a Shopify store to deliver v1 of their product

We have also backed teams where the product is really technical, and the risk is technical rather than market risk.  In those cases, we want to understand how the team sprints and thinks about getting the simplest robust product to launch.

In contrast, there are a lot of teams that spend a lot of time and hard work doing research (market research), surveys, customer interviews, etc.  That’s ok, but most people cannot articulate what product they want or what they will pay for.  From my own operator experience, the best way to learn and iterate is to actually start working with paying customers.

Note: there are a lot of other important things that I didn’t mention: market size and team.  These are going to be really important for other investors.  For me, strength of the problem is usually correlated with market size (not always but most of the time), and execution with speed is correlated with team.

In conclusion, from my perspective, pre-seed doesn’t mean just sitting around with an idea.  To me, it means the beginning stages of building the company and learning and iterating on those learnings quickly.  I am not looking for loads of traction but the ability to have a conversation with a team about what they’ve learned each new week based on something new they tried in their sales or product development the prior week.  And if you can do that week over week, you’ll hit some level of success.

It’s taken me a couple of years to grapple with this but let’s just put this out there: fundraising in the Silicon Valley is very much a game of pedigree.  It’s something that startup investors talk about in vague terms.  Investors say things like: “This founder is very fundable” or “This founder doesn’t pattern match.”  Ellen Pao talks about this explicitly in the excerpt of her new book, Reset:

Predicting who will succeed is an imperfect art, but also, sometimes, a self-fulfilling prophecy. When venture capitalists say — and they do say — “We think it’s young white men, ideally Ivy League dropouts, who are the safest bets,” then invest only in young white men with Ivy League backgrounds, of course young white men with Ivy League backgrounds are the only ones who make money for them. They’re also the only ones who lose money for them.

This is an incredibly telling statement.  As an early stage investor, I know that if I can invest in a team that fits exactly what Ellen describes (or MIT/Stanford, or Facebook/ Google), I’ll win in the short term.  It doesn’t really matter what the team is doing or how well they execute.  I know that some investor down the road is going to be enamored with the team’s resume, pick up that team at a higher valuation, and fund them.  In fact, I’ve seen this happen over and over with my portfolio companies who have pedigree – even with the teams that are not able to execute well!  And since gains in most investors’ portfolios are on paper only and are not realized for 7-10 years, executing on this strategy is a short term win for early stage investors such as myself, even if companies die 5-7 years later!

Knowing that, you have to believe that your portfolio companies can get downstream capital because, as a small investor, you won’t be able to invest at the series A round and beyond to carry your companies forward.  So if you are interested in investing in a company that doesn’t fit the “classic pattern,” then you have to think through all the scenarios if such a company is not able to raise money.  You have to have so much conviction that the company will survive through all the tough years before traction really takes off.  You have to believe that the founders are willing to eat glass for breakfast every day – 100x more than a team that can easily get VC investment.  In other words, the teams I’ve backed who do not have pedigree are 100x more tenacious and stronger than those with pedigree.  I’m aware that the world will treat some of my children more harshly than others simply because of the way they look or sound or where they went to school or didn’t go to school.

It isn’t fair.  But it’s business.  And that’s how things are.  Today.

I’m optimistic the world is changing, and it’s changing at a faster pace than ever before.  Just a couple of years ago, AngelList announced their syndicate feature.  This allowed angel investors to accumulate more fire power behind their small checks.  Gil Penchina, for example, a rainmaker angel investor, could get his 99 friends to invest alongside him, which brings his total investment power to millions of dollars.  This was an incredible innovation in startup investing.  It meant that small investors could essentially band together to lead a series A round.  Small investors could have conviction in companies where traditional VCs do not.

This is just the first step.  By democratizing money – i.e. truly commoditizing money – it means that founders not only need not rely on the 50 or so Silicon Valley VC firms for serious cash, but it also means that a lot of companies that are growing quickly but don’t fit the right “pattern” VCs are looking for will be able to get funded by others who have conviction in their businesses.

Syndicates are logistically challenging.  You have to rally all of your 99 angel friends to participate.  And if they don’t, you still don’t have a lot of fire power alongside your small check.  Frankly, most of the time, your friends are too busy to partake and to be evaluating all these deals, since this is not their full time job.  Moreover, as a founder, often you are limited to only fundraising from one syndicate at a given time, which limits the number of groups of people you can raise from. Moreover, these syndicates are often limited to investors from certain geographies by both legal and practical reasons.  Net-net, syndicates have increased the power of small investors by a lot for some, but for most small investors, they still do not have enough money behind them to be able to lead rounds.

Enter ICOs (initial coin offerings).

The Benefits of ICOs

I’m incredibly bullish that ICOs will really empower all kinds of investors – large and small – to make investments in founders in whom they have conviction without caring if the 50 Silicon Valley VCs will have that same conviction (or if they’re conflicted out).  Although tokens will be subject to securities laws, I think ICOs will provide the following benefits:

1. Greater geographical access.  

In other words, investors from other parts of the world or even within the States (both big and small investors) could partake in fundraising rounds in Silicon Valley and vice versa.  Today many people simply don’t have access to deals being done here in the Valley.

2. More efficient infrastructure.  

Today, there is a lot of friction and just general inefficient infrastructure around deals.  ICOs circumvent problems that you find with traditional banks – wire cutoff times, wire fees, currency exchange rates & fees (to a certain extent), in some cases, legal paper work printed and physically signed. Technology, in general, is a good way to get rid of anachronistic practices.  Why are there wire cutoff times in this day and age?  I’ve been told that some microfunds pick their banking partner partly based on the wire cutoff times.  Shouldn’t everything run 24/7 now?

3. Objectivity in evaluating companies.  

Founders won’t be judged on appearances.  When you walk into a typical VC office today, if you’re tall and have a booming voice, you’re already at an advantage.  Online, none of this matters. No one cares if you’re good looking or can talk well or if you’re tall or if you’re pregnant.  All that matters is that you can run your business well.  This is the promise that I see in ICOs – that you’ll be judged by your execution and merit rather than by how you look and sound.  We’re still VERY FAR OFF from this vision, and many of the pieces that are needed to get to this point don’t exist today. However, this is the direction that I see ICOs going in.  We are living in a new, incredibly fast-paced era for startups, and I am so excited to see the playing field finally start to level out for entrepreneurs everywhere.